‘Sometimes I Wish I Hadn’t Sold’: Why a 40-Year Owner Regrets Her Multimillion Dollar Payout
She spent 40 years building a multimillion dollar business, then sold it and discovered she had no idea what to do next. Her story reveals a trap that catches far more sellers than anyone talks about.
This post may contain links from our sponsors and affiliates, and Flywheel Publishing may receive compensation for actions taken through them.
A few years after she and her husband sold the family business they had spent 40 years building, a client told David Fagan something he says he has never forgotten: “David, sometimes I wish I hadn’t sold.”
Fagan told the story in a recent episode of We Study Billionaires podcast. The sale brought in what he called a “multi, multi million dollar payout.” The deal closed without problems, and on paper the couple had reached their number.
“She had spent 40 years learning how to run her business, but virtually no time learning how to live without her business,” Fagan said. Almost overnight she had to learn yields and withdrawal rates, read broker statements, and field calls from wealth advisors. He called it “very overwhelming for their family at this late, late stage in their life.”
A lot of sellers feel this way. An Exit Planning Institute survey found that 75% of owners “profoundly regretted” selling 12 months after the deal closed. Fagan says anyone who gets a lump sum late in life faces the same pressure, whether it comes from an inheritance, a property sale, or a divorce.
Four Decades of Know-How Turned Into a Portfolio Overnight
Fagan’s rule is frank: “You don’t want to learn investing for the first time when the stakes are the highest.”
For four decades, this owner’s wealth was tied to one asset she knew well. The sale turned it into a portfolio of investments she had never managed. She had to settle on a mix of investments, a safe withdrawal rate, and a capital gains tax bill all in the same year, at an age that leaves little time to recover from an early mistake.
Idle Cash Is the Costliest Safe Choice
The main tension here is that doing nothing feels comfortable but costs money. Fagan has watched people leave large sums in cash for long stretches while they decide what to do. It feels safe. Over time, he says, it becomes one of the most expensive choices they make, because the money loses years of compounding.
Take a hypothetical $5 million payout. A 4% withdrawal rate pays out about $200,000 a year. If that money earns 4% in cash for three years instead of 7% in a diversified portfolio, the gap grows to roughly $500,000. Idle cash has usually trailed a diversified portfolio over multiyear periods.
Two Paths Once the Wire Hits
Park the Money and Figure It Out Later
This is where most overwhelmed sellers end up. Waiting feels careful, but each year of indecision gives up compounding. Panic often follows, and it tends to end with buying high-fee products the seller cannot judge.
Build the Plan Before the Money Arrives
The better path starts 12 to 24 months before closing. Keep one to two years of spending money in cash or Treasury bills. Move the rest into low-cost, diversified funds over six to 12 months. Write down a withdrawal rule and learn three basics:
- How yield differs from total return
- What withdrawal rate your savings can support
- How to read a monthly statement
An advisor is clearly worth the fee in one case. If the proceeds push your estate toward the federal estate tax exemption, now $15 million per person, the estate planning alone justifies a fee-only advisor. (Most estate messes trace back to a stale beneficiary form or an untitled account, and we put the full checklist in a free estate guide here.)
What Buffett Kept When He Stepped Down
On September 18, Warren Buffett, 96, stepped down as board chair of Berkshire Hathaway (NYSE:BRK-B | BRK-B Price Prediction) in a letter to shareholders. He became chair emeritus and remains a director on the board, and he remains active as a shareholder. In that letter, he wrote that he still has “the best job in the world.”
The most famous leadership transition in business was designed to keep the owner’s identity and involvement intact. Buffett gave up a title and kept his board seat, his stake, and his tie to the company. Berkshire’s Class B shares were trading near $500 on last look, and his wealth is still in the business he knows best.
Two Moves to Make Before Your Own Payout
First, if a sale, inheritance, or settlement is coming, start learning about withdrawal rates, investment mix, and statements now, while mistakes are still cheap. One year of preparation before closing beats three years of struggling afterward.
Second, plan your time as carefully as your money. A consulting contract, a board seat, or a mentoring role can give a private owner what the emeritus title gives Buffett. It keeps the payout from feeling like a loss.
Contact [email protected] for any questions or corrections.
Trey has been an editor and author at 24/7 Wall St. for more than a decade, where he has published thousands of articles analyzing corporate earnings, dividend stocks, short interest, insider buying, private equity, and market trends. His comprehensive coverage spans the full spectrum of financial markets, from blue-chip stalwarts to emerging growth companies.
Beyond 24/7 Wall St., Trey has created and edited financial content for Benzinga and AOL's BloggingStocks, contributing additional hundreds of articles to the investment community.
Trey's editorial expertise extends across multiple publishing environments. He served as production editor at Dearborn Financial Publishing and development editor at Kaplan, where he helped shape financial education materials. Earlier in his career, he worked as a writer-producer at SVE. His freelance editing portfolio includes work for prestigious clients such as Sage Publications, Rand McNally, the Institute for Supply Management, the American Library Association, Eggplant Literary Productions, and Spiegel.
Outside of financial journalism, Trey writes fiction and has been an active member of the writing community for years, moderating workshop sessions at regional conventions.
